This paper presents the results of a thorough planning investigation carried out by the Transmission System Operator (TSO) and the Distribution Network Operator (DNO) in Greece in order to study the interconnections of the Aegean Islands with the mainland power system. The feasibility of interconnecting islands is based on the need for a reliable power supply to isolated and autonomous islands, reducing the operating costs of the power generation system through the withdrawal of high-cost oil-fired generating units, and the further ability to increase renewable energy source (RES) penetration in the country’s energy mix, according to directions imposed by the National Energy and Climate Plan. Among the alternative topologies and interconnection technologies considered, the final selection of the interconnection scheme selected for inclusion in the development plans of TSO and DNO was based on their detailed comparative evaluation, considering financial and other technical criteria.